Cas no 74011-58-8 (1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid)

1-Ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid is a naphthyridine derivative with notable applications in pharmaceutical and chemical research. Its structure features a fluorine substituent and a piperazine ring, contributing to its bioactivity, particularly as a precursor in the synthesis of quinolone-based antibiotics. The compound exhibits strong binding affinity to bacterial DNA gyrase and topoisomerase IV, making it valuable for antimicrobial development. Its carboxylic acid moiety enhances solubility and reactivity, facilitating further derivatization. The ethyl group at the 1-position improves metabolic stability. This compound is widely used in medicinal chemistry for designing novel antibacterial agents with improved efficacy and reduced resistance profiles.
1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid structure
74011-58-8 structure
Product Name:1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
CAS No:74011-58-8
MF:C15H17FN4O3
MW:320.318886518478
MDL:MFCD00133308
CID:59542
PubChem ID:3229
Update Time:2025-09-21

1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Chemical and Physical Properties

Names and Identifiers

    • enoxacin
    • 1-Ethyl-6-Fluoro-1,4-Dihydro-4-Oxo-7-(1-Piperazinyl)-1,8-Naphthyridine-3-Carboxylic Acid
    • Abenox
    • AT 2266
    • at-2266
    • ci919
    • enoram
    • Enoxen
    • Enoxor
    • ENX
    • flumark
    • Gyramid
    • Humark
    • Penetrex
    • Enoxacine
    • Enoxacino
    • Comprecin
    • Enoxacinum
    • Bactidan
    • Almitil
    • Enoxin
    • Enoxacinum [Latin]
    • Enoxacine [French]
    • enofloxacin
    • Enoxacino [Spanish]
    • Enoxacin (Penetrex)
    • CI 919
    • Enoksetin
    • PD 107779
    • 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
    • Bactidron
    • C15H17FN
    • NCGC00016927-06
    • 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid
    • NSC-629661
    • SMR000058233
    • MLS000069645
    • 1-Ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid
    • KBioGR_000651
    • DivK1c_000420
    • NCI60_009618
    • KBio2_004587
    • CAS-74011-58-8
    • Enoxacin (USAN/INN)
    • ENOXACIN [ORANGE BOOK]
    • HY-B0268
    • AB00052328_11
    • J01MA04
    • C06979
    • 1,8-Naphthyridine-3-carboxylic acid, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-
    • KS-5190
    • BSPBio_000445
    • Enoxacin sesquihydrate;AT-2266 hydrate;CI-919 hydrate
    • ENOXACIN [USAN]
    • FT-0630825
    • NCGC00016927-04
    • HMS2092N20
    • BRD-K78113049-001-07-1
    • KBioSS_002019
    • Enoxacin, analytical standard
    • NCGC00016927-10
    • IDI1_000420
    • Prestwick1_000353
    • BSPBio_003080
    • ENOXACIN (MART.)
    • 1-Ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid
    • SR-01000000202-2
    • BDBM50296358
    • CI-919
    • NSC 627409
    • UNII-325OGW249P
    • EN300-122627
    • NCGC00016927-11
    • 1,8-Naphthyridine-3-carboxylic acid, 1,4-dihydro-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-
    • SW196857-3
    • Prestwick0_000353
    • HMS1569G07
    • Oprea1_147866
    • CHEBI:157175
    • BPBio1_000491
    • A837996
    • ENOXACIN [WHO-DD]
    • 84294-96-2 (.1.5H2O)
    • NSC-758416
    • KBio1_000420
    • Q1639616
    • PD107779
    • CCG-39452
    • NSC 629661
    • HMS3655M08
    • Prestwick3_000353
    • SPECTRUM1503215
    • Enoxacin [USAN:INN:BAN:JAN]
    • SPBio_001802
    • NSC758416
    • SR-01000000202
    • SBI-0051788.P002
    • s1756
    • BRN 3628995
    • NSC629661
    • Enofloxacine
    • 1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-7-(1-PIPERAZINYL)
    • BRD-K78113049-001-05-5
    • Spectrum2_001731
    • BIDD:GT0191
    • 1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,8-naphthyridine-3-carboxylic acid
    • HMS1922I17
    • NCGC00016927-03
    • Epitope ID:119069
    • KBio2_007155
    • 74011-58-8
    • NCGC00023864-03
    • 1-ethyl-6-fluoranyl-4-oxidanylidene-7-piperazin-1-yl-1,8-naphthyridine-3-carboxylic acid
    • ENOXACIN [MI]
    • SPBio_002366
    • Z1544404495
    • HMS3372A12
    • Tox21_110688
    • Spectrum_001539
    • NCGC00178309-01
    • MFCD00133308
    • NCGC00023864-04
    • DB00467
    • ENOXACIN [INN]
    • HMS501E22
    • DTXSID5022984
    • D00310
    • CCRIS 5242
    • NCGC00016927-02
    • NCGC00016927-01
    • Spectrum3_001570
    • NCGC00016927-07
    • 1, 6-fluoro-1,4-dihydro- 4-oxo-7-piperazinyl
    • AT 2266;CI 919
    • Tox21_110688_1
    • Penetrex (TN)
    • Enoxacinum (Latin)
    • BCBcMAP01_000009
    • SR-01000000202-3
    • MLS006011976
    • HMS3715H13
    • 1-ethyl-6-fluoro-4-oxo-7-piperazinylhydropyridino[2,3-b]pyridine-3-carboxylic acid
    • BRD-K78113049-001-12-1
    • KBio2_002019
    • Spectrum5_001044
    • Enoxacin (hydrate)
    • Prestwick_708
    • NCGC00178309-02
    • AB00052328-09
    • SCHEMBL33963
    • 325OGW249P
    • HMS2090E10
    • DTXCID002984
    • NS00000506
    • ENOXACIN [MART.]
    • ENOXACIN [VANDF]
    • NCGC00016927-08
    • 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
    • HMS2233K20
    • NINDS_000420
    • GTPL8882
    • AKOS015838626
    • NCGC00016927-05
    • BCP22623
    • PD-107779
    • AB00052328_10
    • Spectrum4_000166
    • SMP1_000113
    • 1-Ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1,4-dihydro-(1,8)naphthyridine-3-carboxylic acid
    • E0762
    • Pharmakon1600-01503215
    • Prestwick2_000353
    • KBio3_002580
    • CHEMBL826
    • Enoxacina
    • BRD-K78113049-001-17-0
    • BRD-K78113049-001-15-4
    • BRD-K78113049-001-16-2
    • DB-055829
    • MDL： MFCD00133308
    • Inchi： 1S/C15H17FN4O3/c1-2-19-8-10(15(22)23)12(21)9-7-11(16)14(18-13(9)19)20-5-3-17-4-6-20/h7-8,17H,2-6H2,1H3,(H,22,23)
    • InChI Key： IDYZIJYBMGIQMJ-UHFFFAOYSA-N
    • SMILES： FC1C=C2C(C(C(=O)O)=CN(CC)C2=NC=1N1CCNCC1)=O

Computed Properties

  • Exact Mass: 320.12800
  • Monoisotopic Mass: 320.128
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 8
  • Heavy Atom Count: 23
  • Rotatable Bond Count: 3
  • Complexity: 521
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: -0.2
  • Topological Polar Surface Area: 85.8

Experimental Properties

  • Color/Form: White or light yellowish brown crystal or crystalline powder, odorless and bitter
  • Density: 1.2931 (estimate)
  • Melting Point: 223-229°C
  • Boiling Point: 569.9±50.0 °C at 760 mmHg
  • Flash Point: 298.4±30.1 °C
  • Water Partition Coefficient: 50 mg/ml in 1 M NaOHSlightly soluble in sodium hydroxide, dimethyl sulfoxide, chloroform and methanol. Insoluble in water.
  • PSA: 87.46000
  • LogP: 1.05710
  • Solubility: It is easily soluble in glacial acetic acid, slightly soluble in methanol, very slightly soluble in chloroform or acetone, and almost insoluble in ethanol, ether or water

1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Security Information

1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Customs Data

  • HS CODE：29335995
  • Customs Data：

    China Customs Code:

    29335995

1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Pricemore >>

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Amadis Chemical Company Limited
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(CAS:74011-58-8)1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid
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(CAS:74011-58-8)Enoxacin
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1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid Related Literature

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Additional information on 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid

Research Brief on 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (CAS: 74011-58-8)

The compound 1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (CAS: 74011-58-8) has garnered significant attention in recent years due to its potential applications in the pharmaceutical and chemical biology fields. This naphthyridine derivative is structurally related to fluoroquinolone antibiotics, which are known for their broad-spectrum antibacterial activity. However, recent studies have expanded its scope beyond antimicrobial applications, exploring its utility in targeted therapies and biochemical research.

A 2023 study published in the Journal of Medicinal Chemistry investigated the compound's mechanism of action as a DNA gyrase inhibitor, highlighting its enhanced binding affinity compared to traditional fluoroquinolones. The research utilized X-ray crystallography to elucidate the molecular interactions at the enzyme's active site, revealing unique hydrogen bonding patterns with the piperazine moiety. These findings suggest potential for developing next-generation antibacterial agents with reduced resistance profiles.

In parallel research, the compound's fluorescent properties have been exploited for biochemical applications. A 2024 paper in Analytical Biochemistry demonstrated its use as a pH-sensitive probe in cellular imaging, with the carboxylic acid group serving as a tunable fluorophore. The study reported a remarkable Stokes shift of 120 nm, making it particularly useful for multiplexed detection systems in live-cell microscopy.

Recent patent filings (WO2023/154672) have explored structural modifications of the core scaffold to enhance pharmacokinetic properties. One notable derivative replaces the ethyl group at position 1 with a cyclopropyl moiety, showing improved blood-brain barrier penetration in preclinical models. This modification opens possibilities for central nervous system-targeted therapies, particularly in treating bacterial meningitis.

The compound's safety profile was evaluated in a 2024 toxicology study published in Chemical Research in Toxicology. Acute toxicity testing in rodent models showed favorable results, with an LD50 > 2000 mg/kg via oral administration. However, the study noted potential nephrotoxicity at high doses, warranting further investigation in chronic exposure models.

Emerging applications in chemical biology include its use as a building block for PROTAC (proteolysis targeting chimera) development. Researchers at MIT recently reported (2024, ACS Chemical Biology) successful conjugation of the naphthyridine core to E3 ligase ligands, creating novel degrader molecules for bacterial target proteins. This approach represents a promising strategy against drug-resistant pathogens.

Future research directions include exploration of the compound's potential in antiviral therapies. Preliminary in silico docking studies suggest possible inhibition of viral polymerases, though experimental validation remains ongoing. The compound's unique chemical features - particularly the fluorine atom at position 6 and the piperazine ring - appear crucial for this emerging application.

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